3-(Chloromethyl)-5-(3,5-difluorophenyl)-1,2,4-oxadiazole → 4-Chloro-1-{[5-(3,5-difluorophenyl)-1,2,4-oxadiazol-3-yl]methyl}-2-propyl-1H-indole-5-carbonitrile

HRID 913596Notes

Reaction equation

HRID 913596 reaction equation
[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH2:13][CH2:14][CH3:15])[NH:6]2.Cl[CH2:17][C:18]1[N:22]=[C:21]([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[C:25]([F:30])[CH:24]=2)[O:20][N:19]=1>>[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH2:13][CH2:14][CH3:15])[N:6]2[CH2:17][C:18]1[N:22]=[C:21]([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[C:25]([F:30])[CH:24]=2)[O:20][N:19]=1

Participants

3

Reactant 2

HCID 431202093-(Chloromethyl)-5-(3,5-difluorophenyl)-1,2,4-oxadiazoleHCID 674043384-chloro-2-propyl-1H-indole-5-carbonitrile

Product 1

HCID 578000724-Chloro-1-{[5-(3,5-difluorophenyl)-1,2,4-oxadiazol-3-yl]methyl}-2-propyl-1H-indole-5-carbonitrile

Procedure

Synthesized as described in Example 4 from 4-chloro-2-propyl-1H-indole-5-carbonitrile and 3-(chloromethyl)-5-(3,5-difluorophenyl)-1,2,4-oxadiazole: 1H NMR (400 MHz, DMSO-d6) δ 7.95 (s, 1 H), 7.80-7.61 (m, 4 H), 7.57 (d, J=8.5 Hz, 1 H), 5.83 (s, 2 H), 3.05-2.75 (m, 2 H), 1.70-1.41 (m, 2 H), 0.92 (t, J=7.3 Hz, 3 H); MS (ES) m/z 413 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-ab8e52478c4f46e7aea996d668c238ed
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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